


Love in Disguise

by sleepypercy



Category: Supernatural
Genre: Dean in a red wig and fishnets, Dean's freckly belly, M/M, Sam perving on his brother, Sex, Transvestite Hookers, bottom!Dean
Language: English
Status: Completed
Published: 2015-06-21
Updated: 2015-06-21
Packaged: 2018-04-05 10:24:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,874
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4176303
Author URL: https://archiveofourown.org/users/sleepypercy/pseuds/sleepypercy
Summary: <blockquote class="userstuff">
              <p>In order to catch a CEO that's been cutting out hearts, Dean reluctantly poses as a transvestite hooker. Sam never expected his brother to look so good in that skirt.</p>
            </blockquote>





	Love in Disguise

**Author's Note:**

> Thanks to my guard dragon, [](http://saltandburnboys.livejournal.com/profile)[saltandburnboys](http://saltandburnboys.livejournal.com/) for beta'ing this for for me.

“Dean, come on! I looked ridiculous. Could you at least _try on_ the skirt before you say ‘no’?”

Growling, Dean yanks the short black material out of Sam’s hands, shaking his head. “If Dad knew what we were up to—”

“If Dad would ever _bother_ to answer his damn phone,” Sam interrupts, “then maybe I would care what the man has to say. But since he’s still blowing in the wind somewhere, you and I are all we’ve got. So stop whining like a little girl and put on the skirt. And one of those crop tops while you’re at it.”

Pouting and mumbling under his breath, Dean closes the dressing room curtain and slips into the velvet mini-skirt and front-tie shirt, knotting together the loose ends like he thinks he’s supposed to do before he steps out and prepares to take his brother’s ridicule. Because he already knows he looks awful. Why did they ever think they could pull this off?

“Yeah, I know. I look stupid,” he says, waiting for Sam to start in with the teasing. “Go on, get it all out, Sammy. I gave you enough crap when it was your turn to play Hooker Barbie.” He can see himself in the mirror, and there’s no way he’s passing as a girl, not with his jawline and obvious lack of boobs. Sam, however, hasn’t said anything yet, is just blinking at Dean with an odd look on his face, and Dean looks down at himself, not quite sure whether Sam’s reaction is approving or not. “Well?” he prompts after a moment, flopping his hands up and down. “Should we try to break into that CEO’s house instead? Because apparently neither one of us can pull off the _sweet transvestite_ look.”

Sam manages to pull himself out of whatever temporary trance he’d been in to shake his head. “There’s no way we can get through his high-tech security,” Sam says firmly. “It’s locked down tighter than the Pentagon. And we can’t get him during the day, either, not with his two bodyguards on constant duty.” Taking a deep breath, Sam finally looks away, small smile on his face, and tosses his brother a dark red wig. “Besides, Dean. A little lipstick, some heels maybe, and this just might work.”

+++

Once Dean’s back in his regular clothes, Sam breathes a sigh of relief. His brother’s features have always skated the line of androgynous, undeniably masculine in almost every way but a few key areas. Soft lips. Dark lashes. Smooth skin. The hooker outfit hadn’t magically transformed Dean into a girl, but it still managed to flatter his body, putting those curved legs and cut hips on display, making Sam want to run his fingers across freckles and muscle.

The car ride back to the motel is quiet, and Sam can tell Dean’s mind is on the plastic store bag in the seat behind them, filled with velvet, fishnet thigh highs, and bright red strands of synthetic hair. Trust Dean to take the most ridiculous _Pretty Woman_ hooker outfit and and still make it hot.

Dean’s attractiveness is something Sam had recognized long ago, cognizance hitting almost the exact moment he hit puberty and could smell the sex across all three feet between their motel beds.

Seeing his brother in that outfit kicked up old memories that have been sitting in the back of Sam’s brain, nudged out like hornets from a nest, zipping around angrily and impossible to ignore. Memories that leave Sam flushed and embarrassed now. From the moment Dean came to pick him up from Stanford, Sam’s been wanting to ask his brother if he _remembers_. If Dean still thinks about all the ways he’d let a then-teenaged Sam experiment, using his big brother as an outlet for all those adolescent hormones that drove Sam crazy with undirected frustration and wanting.

There had never been anyone else for Sam, and he’s not sure if their nomadic lifestyle or mutual unhealthy codependence is to blame, but all Sam had known at the time was that he loved his brother in every way possible. There had been a few half-hearted attempts with some girls, even some boys, but it never felt the same.

Instead, Sam would end up crawling across that three-foot gap, running his mouth across his brother’s neck, rubbing himself against Dean’s thighs and slipping his hand down Dean’s pants so he could hear his brother’s stuttered breathing because Sam didn’t want to be the only one. He always half-expected Dean to shove him away, tell him ‘no,’ but it never happened, and Sam didn’t stop. Not until he finally left for good.

That was, however, years ago, and Sam knows he should try to move on. Should, at the very least, not think about those things while they are in the middle of investigating a string of missing hearts and a CEO who turned security into an Olympic sport. It’s difficult to stay focused on the hunt, though, while thinking about the way that top had displayed Dean’s belly. The soft curve just underneath the knot. The way the pelvic bone peeked around the hips and pointed down below the skirt. Beneath the short hem, Dean’s legs had been criss-crossed with black nylon, the texture accentuating the narrow thigh muscles that Sam knew from experience could lock down hard around a set of hips. Even a set of narrow ones on a guy who was just barely finishing up puberty.

Sam wonders if Dean ever thinks about how much changing Sam has done at Stanford. Or about how easily Sam had flipped Dean in that short spar, gaining a new advantage over Dean with all that added muscle that had been easier to put on once Sam’s limbs were finished stretching out.

Sam really wants to find out if he could pin Dean to the bed and keep him there, straddling his brother’s hips with his thighs as he holds Dean’s shoulders down with his hands. It’s something he’s simultaneously desperate to find out and afraid to ask.

+++

They scout out the street corner beforehand, going at night so they can assess the local competition. Most of the other boys keep their distance, wary of strangers who don’t seem interested in picking up a date. But one of the boys won’t take ‘no’ for an answer and keeps slinking around Sam like a half-naked alleycat while tossing out invitations, his prices dropping lower and his suggestions growing dirtier with every rejection.

Dean seems to find Sam’s discomfort amusing, letting Bambi – as the kid insists they call him – in on a few of Sam’s extra-sensitive areas and preferences in bed. “Focus on the balls,” Dean suggests, throwing a wink in. “He might drop you a twenty if you offer to suck on his jewels.”

Glaring at his brother, Sam attempts several times to extract Bambi’s fingers from his belt loops, letting him down with a “sorry, not interested” while Dean grins at them both.

“Look, we’re just trying to find a guy who likes to drive by here,” Sam says exasperatedly, backing up a couple paces. “Have you seen a dark town car come out this way? Guy named Keller inside, salt-and-pepper hair, scar over his mouth?”

“Yeah,” Bambi says with a nod, eyes lighting with recognition. “Yeah, I’ve seen him a time or two. The boys who go with him come back maybe nine times outta ten. Pays well, though, if you’re willing to risk it.” His pink lips part as he lets his eyes drag over Sam’s body, tongue peeking out to lick across his lips when his gaze lowers to Sam’s crotch. “Twenty bucks’ll get you a blow job and his type.”

“How about just the information and we’ll call it thirty,” Sam counters with a tight-lipped frown.

Bambi sighs and rolls his eyes dramatically but ultimately takes the offer, stuffing the bills into the front of his short jean skirt, eyes on Sam as he snaps the band back into place and suggestively rotates his pelvis a few times.

“He likes ‘em pretty,” Bambi says, eyes flicking over to Dean. “Which you got no problem with. Although you’re a little too butch for him. I don’t know who you think you’re foolin’, but you gotta relax. Stop looking like you’re gonna punch the next guy who looks at those cotton candy lips.”

Dean throws Bambi a dirty look, but Sam puts a hand on his shoulder. He can feel his brother fighting against his instincts, violent reactive tendencies born from too many men pinching Dean’s chin in their fingers and making assumptions about what those lips could do. It’s too easy for them to underestimate the strength behind the long lashes and plush lips. Thankfully, Sam can feel Dean relax under his touch, remembering that they’re on a job and Bambi’s nowhere near being a threat. Also, it’s not the first time Dean’s had to use that pretty face to his advantage.

“Fine,” Dean grumbles in resignation. “Show me.”

+++

The next night, Dean’s leaning against the side of a building, dressed up in the outfit they’d picked out just a couple days ago, peach gloss on his lips and his wig firmly in place. He’s staring to the side, aloof look in his eyes, hips cocked out and lips pouted. After an hour or so of coaching, Dean manages to look natural and comfortable, and if Sam didn’t know his brother so well – didn’t catch on to the fingers tapping anxiously against his hip – he would have sworn that Dean had been doing this all his life.

Sam’s currently waiting in the Impala, tucked into a one-way side street that gives him a decent view of the boulevard. It’s difficult watching his brother like this, though. A few cars have already pulled up in front of Dean, engines idling while they try to lure Dean closer, upping whatever offer he’s refusing until they finally understand that Dean’s not going to get in the car. Most of them move on, disappointed and resigning themselves to finding an ersatz willing body for the night. A few of them spit out nasty names at Dean before speeding off, too disgruntled to even bother finding a poor substitute.

Finally, Mr. Keller pulls up with his driver. Window rolled down, he surveys the street like he’s not sure anyone’s really worth his time. But Sam can see the way the man’s eyes keep snapping back to his brother, drawn to that unconscious sexuality that had fourteen-year-old Sam completely bewitched. Dean’s the best piece out there and they all know, and it doesn’t take long before the man holds out his hand and gestures for Dean to come over.

Somehow Dean manages to walk over without face-planting into the cement. He’s definitely not used to heels, but they need to sell this, and Dean only has to walk ten feet from the corner to the car. He wobbles a bit but manages not to let it affect his hip-swaying strut, leaning an arm against the window when he gets close enough and cocking out his hip in an obvious parody of what Dean thinks street walkers look like when they’re arranging a date.

Sam can’t help tilting his head, teeth scraping across his bottom lip as his eyes trace the shape around Dean’s back and down his legs. The heels force Dean’s posture up, and his ass has never looked better, muscles tight and perky as he bends over.

After a brief exchange of words, Dean’s invited inside, and he slides himself onto the leather bench seat. As soon as the door shuts, Sam throws the Impala into drive and follows them, trying to remain inconspicuous without losing his brother.

+++

It feels like a bad joke gone too far when Dean finds himself coaxed to the wide floor of the CEO’s spacious car. He tries to talk as little as possible, letting his cocky smile speak for itself when Mr. Keller’s fingers press into Dean’s jaw and he asks if that mouth feels as good as it looks.

Dean is supposed to wait until they get to Mr. Keller’s apartment. There’s a good chance that the man arranges his organ-selling business inside his home, and Sam really wants to get a look at Mr. Keller’s laptop and financial books. Unfortunately, things are already moving much faster than Dean had anticipated, and his pulse kicks into overdrive as he realizes just how many things Mr. Keller might expect him to do before they even reach the apartment building.

“Pull me out,” Mr. Keller orders softly. Gulping back his anxiety, Dean takes in a deep breath and focuses on staying in character. He can’t afford to botch this now.

He rubs his hands against the bulge beneath the man’s dress pants, letting his mouth part with a soft wet sound as he leans in, breathing warm air against the zipper.

“How do you want me to do it, baby?” Dean asks, voice soft and breathy. The words sound dirty in his mouth, especially while he’s kneeling between a set of thick thighs, and he tries to ignore the hot, embarrassed thrill flushing up his skin.

“Use your hands.”

Dean swears that he can see a flash of sharp teeth behind the man’s grin. Working against every impulse screaming at him to tear this monster’s head off, Dean pinches the man’s zipper between his fingers and pulls down, revealing a hardening cock threatening to slip through the slit of a pair of blue silk boxers. At a nod from Mr. Keller, Dean draws it out then leans in to run his tongue up the sides, holding it up so he can get a good lick around the head.

“Go slow,” the man murmurs with a soft groan of appreciation as he grabs onto the back of Dean’s head, fingers tight in his hair. It’s uncomfortable but not yet threatening, so Dean ignores the tug against his roots and continues sliding his tongue around while the man mutters more filthy directions. “Get my dick nice and wet. Make it ready to slip into your ass when we get to my place.”

Dean leans in to take another lick then yelps as his head gets yanked back.

Mr. Keller looks like he’s about to say something but then pauses, eyes glancing down. “Look at all those goddamn freckles,” he mutters absently, using his free hand to trail a finger down Dean’s throat. Dean hates how vulnerable he feels with his neck bared like this, but he keeps reminding himself that the apartment’s just a few miles down the road. He should only have to blow the guy for a few more minutes until they reach the building.

After a minute of reverie, the man’s gaze goes back to Dean’s eyes, and he tugs harder. “Keep those pretty green eyes on me when you’ve got my cock in your mouth,” he orders, and Dean pauses for a second to simmer, imagining, with some satisfaction, putting a bullet between the CEO’s dark eyes. But Sam’s counting on him, along with any number of potential future victims who’d prefer keep their hearts in their chests, so after a quick breath in, Dean nods slightly and leans down again, this time keeping his chin tilted up.

It’s difficult but not impossible to run his tongue around the man’s prick as he obediently stares up, and as soon as he’s run his tongue along every side, Dean traces the cockhead around his lips, smearing precome and lipgloss together. He can feel the organ twitch against his mouth in appreciation as Mr. Keller huffs out a quick aroused grunt along with a hissed, “So fucking pretty,” which Dean assumes is aimed at him and his lips.

When he can’t put it off any longer, Dean opens his mouth and slips the dick down his throat, trying to take it slow so he can breathe through his nose. But Mr. Keller’s too excited, and his fingers tighten in Dean’s hair as he slams his hips forward, choking Dean so quickly and completely that his eyes start to water. Clawing at the man’s thighs, Dean tries to push himself back. He’s taken cock before, but this is too much at once and he can’t breathe.

“Don’t you dare pull back,” Mr. Keller threatens, thrusting even deeper. “You will take what you’re given, whore.”

Eyes narrowed in irritation, Dean can feel his anger build and he lets all that adrenaline surge until he shoves at the solid body in front of him, pushing hard enough to jolt Mr. Keller back and snap his head loudly against the back of the seat. The man’s hands lose their grip and slip from around Dean’s head.

After a few deep gasps for air, Dean coughs out the taste of the man’s unwashed prick, wrinkling his nose as he reaches behind himself to pull out the glock he had tucked into the back of his skirt. “How about you take this instead,” Dean says in a low, raspy voice, moving the weapon to aim right over the man’s werewolf heart.

+++

Sam jumps when he hears the gunshot and grows worried when the car he’s been tailing is suddenly wrenched over to the side of the road. He’s already throwing the car into park when he hears another gunshot followed by the side door being thrown open.

His gun is drawn and ready as soon as he jumps out of the car, but the second he sees his brother stumble out, he drops his arm to the side, flicking the safety back on in relief. His eyes grow wide when he takes in the blood covering his brother’s face and clothes, but Dean gives him a watery smile and shakes his head.

“It’s okay, Sammy,” he assures him. “S’not my blood.”

“What happened?” Sam demands, but Dean ignores him, his high heels clicking on the sidewalk as he hurries to the Impala and tucks himself inside. Sam quickly slides into the driver’s side, ready to demand more answers, but Dean makes an impatient motion towards the steering wheel.

“Hit the gas, Sam. Police are probably already on their way.”

Saving his questions for a more appropriate moment, Sam obligingly maneuvers the car back on the road, taking a few backroads as a safety precaution. When they’re on the main road, Sam glances over at his brother, watching him swiping at the blood on the face with one of the wet wipes they keep stashed in the glove compartment.

“The guy was getting handsy,” Dean says defensively at Sam’s disapproving expression.

“Well, he did think you were a hooker,” Sam points out. “Might explain him treating you like one.”

“Yeah, well, he violated my ‘no kissing on the mouth’ policy,” Dean dryly answers, tossing the used, bloody wipe into the plastic grocery bag they’ve been using for trash. “That and he tried to asphyxiate me with his cock.”

Sam winces at that, shooting his brother another quick look and noticing the way Dean’s lipgloss has smeared across his chin. The tendrils of something protective stir in his chest, and Sam tries to tamp it down before it reshapes into something dangerous.

“And the driver?” Sam asks, remembering the second shot.

“He started to turn. Guy must have had some canine blood in ‘im too.”

Despite Dean being more than capable of taking care of himself, Sam really hates it when his brother goes rogue. It just gets worse every time Dean gets away with it, walking away with that stupid cocky smile of his and looking proud of the blood splattered across his face like he thinks he’s Sylvester freakin’ Stallone. Sam’s certain Dean’s gonna get himself killed one day, thinking he can take on the world and cheat death.

“Hey, it wasn’t a problem,” Dean assures Sam when he sees his dark expression. “I popped ‘em both before they could even scratch me. As far as I’m concerned, this was a win.”

Sighing, Sam slots the Impala into an empty parking spot in front of their motel room, and Dean pushes open the door and balances himself on those gigantic high heels. Sam tries not to watch, but he can’t help himself. There’s something about Dean in that outfit, and it’s not just the exposed skin or the way the material clings to his body. Something about those clothes makes Dean look vulnerable and willing, like he’d suck down Sam’s cock and be grateful for the chance.

Sighing, Sam scrubs a hand across his face, wondering if he’s just tired. But his brother catches him looking and grins.

“I was just getting the hang of these things, too,” Dean says as he takes a few exaggerated sashays around the car. “Bet pretty soon I coulda been charging double Bambi’s asking price.” Sam grins and rolls his eyes, about to suggest that Dean keep the outfit for whenever they’re hard up on cash, when they hear a catcall whistle bounce across the covered walkway, followed by an echoing request to, “Bring that ass over here, sweetheart.”

Dean’s shoulder tense, jaw tight like he’s deciding if it’s worth his time to start throwing punches. Sam, for his part, is too grumpy and tired to even consider just ignoring the asshole. Throwing a glare towards the offender, Sam slides next to his brother and flings an arm around his shoulders, ignoring the part of him that knows he’s acting stupid. “His ass is taken for the night,” Sam growls, leading Dean towards their door. If he’s a little too pushy as he ushers Dean inside and slams the door shut, he figures no one else needs to know.

“Slow down there, Romeo,” Dean laughs, but Sam crowds him against the wall, shoving his face against the side of Dean’s neck. It’s disconcerting, the way Dean’s three-inch heels even out their heights, but it also makes it easier for Sam to nose into Dean’s shoulder and breathe in.

“You look so stupid,” Sam says into his brother’s neck. “So, so stupid, and so fucking hot.”

Dean goes still, and Sam worries that he’s crossed a line. But then Dean’s hand slips under Sam’s shirt, fingers sliding haltingly across across the bone of his hip. A subtle invitation, but one that Sam’s more than happy to accept.

He pulls back just long enough to thumb over Dean’s smeared mouth then leans in to kiss him, vision blurring when Dean pushes back eagerly, mouth hot and wet against Sam’s.

“Thought we were done with this,” Sam says between frantic kisses, dizzy and stupid because he’d forgotten just how addictive his brother is.

“You’re the one that left,” Dean reminds him, although there’s no malice in the tone. “I’ve been waiting for this since I grabbed you in California.”

Sam can feel Dean’s fingers slipping underneath his pants, pulling at the belt, and he knows Dean’s ready to give him whatever he wants, just like he’d always done. But Sam doesn’t want what he had before — he doesn’t want fumbled, adolescent rutting while Dean lies back and takes whatever Sam wants to give. He’s had years to realize just what he wants, and it’s a lot more than that.

Instead, he falls to his knees, hands traveling down Dean’s body until they’re resting on his hips. The knot of the crop top is sitting at the base of Dean’s sternum, showing off golden skin dotted with cinnamon belly freckles. They’ve been making Sam’s mouth water all night, and, naturally, that’s where he starts. Leaning in, he presses his tongue flat just above the band of the skirt, licking up the ginger happy trail, over Dean’s belly button, and — while leaning higher on his knees, fingers circled around Dean’s wrists — ending at the thick knot.

When Sam loosens his grip, Dean’s hands drop to rest on top of Sam’s hair, and Sam murmurs approvingly. “Go ahead. Pull it,” he encourages, breath skating across the curve of Dean’s belly.

Warm fingers card through Sam’s hair, tightening intermittently, and the pain feels good, a dull pressure that zaps across Sam’s skull. The sensations all pool into Sam’s groin, making him shift his hips in circles as his tongue traces the shape of Dean’s stomach. He’s always loved this part of Dean, long before his hormones ever kicked in.

He used to seek it out specifically whenever he had a nightmare, nuzzling under Dean’s pajama shirt until he’d get to that warm patch of skin. Dean would wake up and blearily murmur something about Sam’s hair on his ticklish skin, but he’d never pushed him away. He’d just sigh and pull him closer, letting Sam fall asleep to the rise and fall of Dean’s breathing.

Possession over that space starts to kick in, and Sam pauses to mouth a few pink and purple bruises, drawing skin behind his teeth and sucking up salt and sweat. He can feel Dean’s erection start to press against his chest, and Sam pulls back to appreciate the way it’s tenting Dean’s skirt. Licking his lips, he pushes the black velvet up, eyes going wide when he sees what’s underneath.

“When… did you get these?” Sam asks, running his fingers over the black silk panties covering a swollen, leaking penis while his brother shivers at the contact.

“Same time as all the other stuff.” Dean’s ears are turning pink and he quickly adds, “It was go big or go home, Sammy. It was a guarantee that guy was gonna want to strip me down at some point.”

Sam doesn’t bother answering, too turned on at the moment, and he can see the shape of Dean’s hard cock through the silk. There’s a wet spot at the top where its been dripping precome, soaking a dark circle just to the right of a tiny bow.

Leaning in, Sam mouths against the slip-slide material, sucking and wetting it until the rounded shape of Dean’s dick is even more prominent. Mouth going lower, he hooks a finger under the band around the right leg and lets one of Dean’s balls slip out, laving it with his tongue while Dean’s head thunks back on the wall and he mutters nonsense.

As one of his fingers skates back to circle the rim of Dean’s hole, Sam regretfully thinks of the lube stashed all the way in the bottom of his duffle. He hates to walk away, even for a moment, but he needs to get inside his brother right now. He can feel the pressure in his dick, ready to push inside Dean’s warm, ready body. Just as he’s about to get up, Dean’s stance widens and he reaches down to run a hand along the top of his thigh highs. His fingers emerge with a packet pressed between them, and he hands it to Sam, looking somewhat embarrassed.

“Didn’t know what I’d need on the job.”

Sam blinks at the packet in his fingers, eyes taking in the logo and contents. It’s lubricant. That Dean had stored in his fishnet stockings.

“Take off your shoes,” Sam says, voice a little shaky because he doesn’t think he’s ever been more turned on in his life. He waits until Dean’s eyes focus on his to add, “And turn around, ass out.”

The moment Sam’s slick fingers prod against Dean’s hole, Dean pitches forward, catching himself against the wall with his hands. Sam’s never done this before with Dean, never knew how much he twisted and keened while being stretched open and stuffed full. He can feel his dick twitch as the sounds emanating from Dean rise in pitch, and one of Sam’s fingers stretches just a little further to prod against the spongy tissue that makes his brother gasp and push back into the touch. He places his other hand on the spinal curve of Dean’s lower back, where it’s warm and wet with sweat, as he works open a space inside Dean for himself.

After a few minutes, Dean drops his forehead to the wall and chokes out: “Fuck me. Now.” The white noise inside Sam’s head has pushed out every other thought but that one anyway, and Sam lets his fingers slip out.

Loosening his belt and pushing his pants just low enough to free his cock, Sam fills the empty space with his dick, eyes squeezing shut at how tight and hot his brother feels inside. His brother’s a writhing, whining mess beneath him, shoving back in time with Sam’s rhythms, encouraging Sam to go faster, harder, deeper.

By the time Sam thinks to reach down, it only takes the brief brush of his hand to make Dean come, spilling across Sam’s hand and up his belly. Sam’s only lasts a couple more thrusts, both his arms curling around Dean’s chest while he fills him up, panting into his neck.

They both collapse on the floor, Dean stretching out and Sam finding his way to Dean’s belly, which he discovers still molds around his cheek in the perfect pillow.

“Next time,” Dean mumbles as he pets tiredly at Sam’s hair, “You get to be the one in the hooker outfit.”


End file.
